Day: June 9, 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 4595-60-2, name is 2-Bromopyrimidine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C4H3BrN2

INTERMEDIATE 8; Step A; A 3-neck round bottomed flask equipped with an addition funnel and condenser and containing zinc dust (2.45 g, 37.4 mmol) was flame dried. After cooling, and purging the system with nitrogen gas, 6 mL of THF was added, followed by 1,2-dibromoethane (0.298 mL, 3.46 mmol). The mixture was warmed to a vigorous reflux using a heat gun and stirred at reflux for 30 seconds (gas evolution was observed), then cooled to room temperature. The warming and cooling was repeated two more times. Then chlorotrimethylsilane (0.402 mL, 3.17 mmol) was added and the mixture was stirred at room temperature for 20 minutes. N-t-butoxycarbonyl-4-iodo-piperidine (known: Billotte, S. Synlett (1998), 379, 8.97 g, 28.8 mmol) in 15 mL of THF was added over a period of about 1 minutes. The reaction mixture was stirred at 50 C. for 1.5 h, then was cooled to room temperature. Meanwhile, a mixture of tri-2-furylphosphine (267 mg, 1.15 mmol) and Tris(dibenzylideneacetone)-dipalladium(0) chloroform adduct (298 mg, 0.288 mmol) was dissolved in 6 mL of THF under a nitrogen atmosphere, stirred for 15 minutes at room temperature, and added to the organozinc solution. Then a solution of 2-bromopyrimidine (5.50 g, 34.6 mmol) in a mixture of 58 mL of THF and 20 mL of N,N-dimethylacetamide was added. The reaction mixture was warmed to 80 C. and stirred for 3.5 h, then was cooled to room temperature and stirred for 36 h. The reaction mixture was filtered through celite and the filter cake was washed with ethyl acetate. The filtrate was diluted further with ethyl acetate, and washed with saturated NaHCO3 solution. The aqueous layer was back extracted with ethyl acetate, the organic layers were combined and washed twice with water and once with brine. The organic phase was dried over anhydrous MgSO4, filtered, and concentrated. Purification by flash chromatography (silica, stepwise gradient: 25% ethyl acetate/hexane, 40% ethyl acetate/hexane, 60% ethyl acetate/hexane, 80% ethyl acetate/hexane, 100% ethyl acetate) to afford 4.92 g of pure 4-(2-pyrimidyl)-piperidine product (65%). 1H NMR (500 MHz, CDCl3): delta 8.70 (d, J=5.0 Hz, 2H), 7.16 (app t, J=4.5 Hz, 1H), 4.24 (br s, 2H), 3.05 (m, 1H), 2.89 (br m, 2H), 2.01 (br d, J=13 Hz, 2H), 1.84 (dq, J=4.5, 12.5 Hz, 2H), 1.49 (s, 9H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 4595-60-2, 2-Bromopyrimidine.

Reference:
Patent; Butora, Gabor; Goble, Stephen D.; Pastemak, Alexander; Yang, Lihu; Zhou, Changyou; Moyes, Christopher R.; US2008/81803; (2008); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 157335-93-8, Adding some certain compound to certain chemical reactions, such as: 157335-93-8, name is 4,6-Dimethylpyrimidine-5-carboxylic acid,molecular formula is C7H8N2O2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 157335-93-8.

Step L 4,6-Dimethyl-5-[(4-methyl-4-{(3S)-3-methyl-4-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazin-1-yl}piperidin-1-yl)carbonyl]pyrimidine To a solution of (2S)-2-methyl-4-(4-methylpiperidin-4-yl)-1-[6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl]piperazine trihydrochloride (100 mg, 0.183 mmol), 4,6-dimethylpyrimidine-5-carboxylic acid (67 mg, 0.22 mmol) in DMF (5 mL) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (97 mg, 0.22 mmol) followed by triethylamine (90 mg, 0.9 mmol). After being stirred at room temperature overnight, a solution of NaHCO3 in water was added. The resulting solution was extracted with EtOAc twice. The combined EtOAc layers were washed with brine, dried over MgSO4 and concentrated. Column chromatography on silica (10-20% MeOH in EtOAc) afforded the title compound (60 mg) as an oil. MS calculated for C28H36F3N5O: (M+H)+ 516; found 516.2.

According to the analysis of related databases, 157335-93-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xue, Chu-Biao; Cao, Ganfeng; Huang, Taisheng; Chen, Lihua; Zhang, Ke; Wang, Anlai; Meloni, David; Anand, Rajan; Glenn, Joseph; Metcalf, Brian W.; US2005/261310; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 171887-03-9, Adding some certain compound to certain chemical reactions, such as: 171887-03-9, name is N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide,molecular formula is C5H4Cl2N4O, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 171887-03-9.

To a solution ofN-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (12 g, 57 mmol) in THF (250 mL) was added Lawesson’s reagent (17.5 g, 43 mmol). The reaction mixture was stirred at 65C for 30 minutes. The reaction mixture was then filtered, and the filtrate was concentrated. The crude yellow solid obtained was triturated using diethyl ether to afford the title compound (10 g, 93.4%) as a pale yellow solid. LCMS (ES+) 186.95 (M+H)+, RT 1.31 minutes (method 1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 171887-03-9, N-(2-Amino-4,6-dichloropyrimidine-5-yl)formamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB PHARMA S.A.; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BROOKINGS, Daniel Christopher; FORD, Daniel James; FRANKLIN, Richard Jeremy; GHAWALKAR, Anant Ramrao; KULISA, Claire Louise; NEUSS, Judi Charlotte; REUBERSON, James Thomas; WO2013/68458; (2013); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 739364-95-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.739364-95-5, name is 2-Methylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid, molecular formula is C8H7N3O2, molecular weight is 177.16, as common compound, the synthetic route is as follows.

DPPA (0.5 mL, 2.31 mmol) and Et3N (1.2 mL, 8.3 mmol) were added at rt to a stirred solution of l-4b (300 mg, 1.69 mmol) in 1,4-dioxane (10 mL). The resulting reaction mixture was stirred at rt for 50 min, then l-3b (500 mg, 2.57 mmol) was added and the reaction mixture was stirred at 100 C for 2 h. When TLC indicated consumption of starting material the reaction mixture was cooled to rt, diluted in water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried (Na2S04), filtered and concentrated. The crude material was purified by CombiFlash (silica gel) eluted with 8% MeOH in DCM. Fractions containing compound were combined and concentrated and the resulting solid was triturated in MeCN (2 x 5 mL) followed by trituration in EtOH (15 mL). and dried which gave the title compound (100 mg, 15%) as a solid. LCMS (ES+) m/z 369.20 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 739364-95-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 38275-57-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 38275-57-9, name is 5-Bromopyrimidine-2-carbonitrile. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-bromopyrimidine-2-carbonitrile (3.0 g, 16 mmol) in MeOH (20 mL) was added concentrated HCl (19 mL). The reaction mixture was heated at 80 C. for 2 h. Upon cooling to rt, a precipitate formed. Filtration provided the desired product as a white solid (2.5 g, 71%). MS (ESI): mass calcd. for C6H5BrN2O2, 216.0; m/z found, 217.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 9.20 (s, 2H), 3.92 (s, 3H).

According to the analysis of related databases, 38275-57-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Janssen Pharmaceutica NV; Ameriks, Michael K.; Rech, Jason C.; Savall, Brad M.; US2014/275096; (2014); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 591-55-9, name is 5-Aminopyrimidine, the common compound, a new synthetic route is introduced below. SDS of cas: 591-55-9

A mixture of 5-ethyl-6-oxo-6, 7-dihydro-5H-1-oxa-s-indacene-7-carboxylic acid ethyl ester (150 mg. 0.6 mmol) and 5-aminopyrimidine (52 mg, 0.6 mmol.) in benzene (40 ml) was refluxed over a Dean-Stark trap for 1 hour. The mixture was cooled to room temperature, diluted with hexanes and the resulting precipitate filtered. The filtrant was dissolved in ethyl acetate (75 ml) and methanol (3 mi) and washed with 1N hydrochloric acid (1 X 5 ml), brine (1 X 5 ml), dried (sodium sulfate) then concentrated in vacuo. The residue was dissolved in methylene chloride (2 ml), diluted with diethyl ether (5 mi) and triturated with hexanes to give 54 mg 5-ethyl-6- oxo-6, 7-dihydro-5H-1-oxa-5-aza-s-indacene-7-carboxylic acid pyrimidin-5-ylamide (31%) as an orange solid, mp 100-3 C.’H-NMR (CDCI3) : No. 8.9 (s, 1H), 8.6 (d, 1H), 8.1 (d, 1H), 7.9 (s, 1H), 7.7 (s, 1H), 7.1 (s, 1H), 6.8 (s, 1H), 4.5 (s, 1H), 3.9 (q, 2H), 1.3 (t, 3H). MS (m/z, %): 321 (M+-1, 100).

The synthetic route of 591-55-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/41957; (2005); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Related Products of 99586-66-0 ,Some common heterocyclic compound, 99586-66-0, molecular formula is C6H5ClN4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

In this example, two different synthesis reactions were performed subsequently in one reaction vessel without exchange of the reaction medium. (0077) 5.0 g (1 1 .3 mmol) of 5-bromo-6-fluoro-2-((2S,4S)-4-hydroxypyrrolidin-2-yl)-3- phenylquinazolin-4(3/-/)-one hydrochloride and 1 .9 g (12.5 mmol / 1 .1 eq.) of (2- methoxypyrimidin-5-yl)boronic acid was provided in a reaction mixture comprising 5.0 mol% PdCI2(dtbpf) and 3.0 eq. NMM in 40 ml (8V) 2% TPGS-750-M in water and 20 ml (4V) THF. The reaction mixture formed a stable emulsion and the reaction was allowed to proceed for 16 h at 50C under stirring. Then 1 .7 g (10.2 mmol / 0.9 eq.) of 2-amino- 4-chloro-6-methylpyrimidine-5-carbonitrile in 10 ml (2V) THF were added to the reaction mixture. After 18 h at room temperature the product 2-amino-4-((2S,4S)-2-(6- fluoro-5-(2-methoxypyrimidin-5-yl)-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)-4- hydroxypyrrolidin-1 -yl)-6-methylpyrimidine-5-carbonitrile was obtained. (0078) (0079) The same reaction performed in conventional organic solvent (e.g. N- methylpyrrolidone) resulted in about 30% side product (structure in bracket) of the Suzuki cross-coupling reaction. This could be reduced to 3% with the use of 2% TPGS- 750-M in water as solvent and THF as co-solvent.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 99586-66-0, 2-Amino-4-chloro-6-methylpyrimidine-5-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; GALLOU, Fabrice; PARMENTIER, Michael; ZHOU, Jianguang; GUO, Pengfei; (27 pag.)WO2017/168303; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Electric Literature of 42754-96-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 42754-96-1, name is 4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine, molecular formula is C5H2Cl2N4, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of 4-(1H-benzimidazol-2-yl)-phenylamine (5) (1 g,0.005 mol) in isopropyl alcohol (25 ml), 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (4) (0.99 g, 0.005 mol) was added and stirred at room temperature for 24 h. After washing the crude solid withisopropyl alcohol, dried to obtain pure [4-(1H-benzimidazol-2-yl)-phenyl]-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-amine (6) aswhite solid; yield: 79%; mp: >300 C; 1H NMR (400 MHz, CDCl3 + DMSO-d6): delta = 9.75 (s, 1H, ArH), 8.13-8.08 (m, 2H, ArH), 7.92 (d, 1H, J = 8.60 Hz, ArH), 7.72 (d, 1H, J = 8.28 Hz, ArH), 7.62 (bs,1H, NH), 7.15-7.13 (m, 2H, ArH), 6.66 (d, 2H, J = 8.72 Hz, ArH), 5.02(s, 1H, NH); 13C NMR (100 MHz, CDCl3 + DMSO-d6): delta = 147.6, 142.5, 132.2, 130.2, 129.3, 129.2, 124.0, 120.8 (ArC); MS (ESI), m/z: 362.7(M++1); Anal. Calcd for C18H12ClN7: C, 59.76; H, 3.34; N, 27.10, Found: C, 59.83; H, 3.32; N, 27.14.

According to the analysis of related databases, 42754-96-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Singla, Prinka; Luxami, Vijay; Singh, Raja; Tandon, Vibha; Paul, Kamaldeep; European Journal of Medicinal Chemistry; vol. 126; (2017); p. 24 – 35;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reference of 3740-92-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.3740-92-9, name is 4,6-Dichloro-2-phenylpyrimidine, molecular formula is C10H6Cl2N2, molecular weight is 225.07, as common compound, the synthetic route is as follows.

A mixture of 80 (0.25g, 1.11mmol) and IPA (3ml) was stirred for a while and then 2M methylamine in THF (1.39ml, 2.78mmol) was added thereto at 0 °C. The resulting mixture was back to room temperature under stirring for overnight. The reaction was quenched by water and then the mixture was extracted by ethyl acetate (30ml x 3). The residue was purified by flash column over silica gel (ethyl acetate: n-Hexane = 1 :4, Rf = 0.18) to afford 84 (0.22g, 90.23percent) as a pale yellow solid. 1H-NMR (300MHz, CDCl3): delta 3.02 (d, J= 4.2 Hz, 3H), 5.09 (br, 1H), 6.26 (s, 1H), 7.42-7.46 (m, 3H), 8.35-8.37 (m, 2H).

The chemical industry reduces the impact on the environment during synthesis 3740-92-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; TAIPEI MEDICAL UNIVERSITY; YEN, Yun; LIOU, Jing-Ping; CHEN, Chun-Han; (70 pag.)WO2017/15400; (2017); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 56181-39-6, name is 5-Bromo-4-chloropyrimidine, the common compound, a new synthetic route is introduced below. Safety of 5-Bromo-4-chloropyrimidine

Step 4: 5-Bromo-4-hydrazinylpyrimidine[0363] A 100-mL round-bottomed flask was charged with a solution of 5- bromo-4-chloropyrimidine (8 g, 25.00 mmol, 1.00 equiv, 60%) in ethanol (50 mL). To this solution was added hydrazine (10 mL, 99%) drop wise with stirring. The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by TLC (MeOH: DCM = 1: 10). The solids were collected by filtration affording 5-bromo-4-hydrazinylpyrimidine as yellow solid (0.83 g, 18%).

The synthetic route of 56181-39-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; KAHRAMAN, Mehmet; SMITH, Nicholas, D.; BONNEFOUS, Celine; NOBLE, Stewart, A.; PAYNE, Joseph, E.; WO2010/88518; (2010); A2;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia